Triphenylphosphine → Tert-butyl 4-(5-bromo-2-chloroquinazolin-8-yloxy)piperidine-1-carboxylate

HRID 2079674Notes

Reaction equation

HRID 2079674 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].[Br:34][C:35]1[CH:44]=[CH:43][C:42](O)=[C:41]2[C:36]=1[CH:37]=[N:38][C:39]([Cl:46])=[N:40]2>C1COCC1>[Br:34][C:35]1[CH:44]=[CH:43][C:42]([O:33][CH:30]2[CH2:31][CH2:32][N:27]([C:25]([O:24][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:26])[CH2:28][CH2:29]2)=[C:41]2[C:36]=1[CH:37]=[N:38][C:39]([Cl:46])=[N:40]2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 866393225-Bromo-2-chloroquinazolin-8-ol

Product 1

HCID 86639323Tert-butyl 4-(5-bromo-2-chloroquinazolin-8-yloxy)piperidine-1-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (2 eq) in THF was added di-terbutylazodicarboxylate (2 eq). The mixture was stirred 15 minutes at ambient temperature under nitrogen atmosphere. To that was added tert.butyl-4-hydroxypiperidine-1-carboxylate (5 eq). The mixture was stirred 15 minutes at ambient temperature followed by addition of 5-bromo-2-chloroquinazolin-8-ol (1 eq). The mixture was stirred overnight at ambient temperature. The reaction mixture was concentrated and the residue was purified by flash column chromatography (25% EtOAc/Hexane) to provide product as a white solid in 90% yield. ES/MS m/z 442.1 (MH+).

Workup

  1. stirringThe mixture was stirred 15 minutes at ambient temperature
  2. stirringThe mixture was stirred overnight at ambient temperature
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by flash column chromatography (25% EtOAc/Hexane)
  5. customto provide product as a white solid in 90% yield

Sources & evidence

ORD record
ord-d33d2626b9e043d5b0615f9fb627985b
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

Loading…